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Triethylamine → HCID 178523839, 화합물

HRID 215997
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HRID 215997 반응식
[OH:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:47][C@H:48]1[CH2:53][CH2:52][N:51]([C:54]([C:56]2[CH:61]=[C:60]([C:62]([F:65])([F:64])[F:63])[CH:59]=[C:58]([C:66]([F:69])([F:68])[F:67])[CH:57]=2)=[O:55])[C@H:50]([CH2:70][C:71]2[CH:76]=[CH:75][C:74]([Cl:77])=[CH:73][CH:72]=2)[CH2:49]1>C(Cl)Cl.C1COCC1>[F:69][C:66]([F:67])([F:68])[C:58]1[CH:57]=[C:56]([CH:61]=[C:60]([C:62]([F:63])([F:64])[F:65])[CH:59]=1)[C:54]([N:51]1[CH2:52][CH2:53][C@H:48]([NH:47][C:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([OH:1])[CH:11]=2)=[O:14])[CH2:49][C@H:50]1[CH2:70][C:71]1[CH:72]=[CH:73][C:74]([Cl:77])=[CH:75][CH:76]=1)=[O:55]
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참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 22869970((2R,4S)-4-amino-2-(4-chlorobenzyl)piperidin-1-yl)(3,5-bis(trifluoromethyl)phenyl)methanoneHCID 178524625HCID 178524625, 화합물

생성물 1

HCID 178523839HCID 178523839, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

To a stirred mixture of 2.52 g (13.32 mMol) 2-hydroxyquinoline-4-carboxylic acid, 2.7 g (15.98 mMol) HOBt (80%), 3.7 ml (26.64 mMol) triethylamine and 3.8 g (18.64 mMol) DCC in 50 ml of CH2Cl2 were added at room temperature 12.3 g (13.32 mMol) [(2R,4S)-4-Amino-2-(4-chloro-benzyl)-piperidin-1-yl]-(3,5-bis-trifluoromethyl-phenyl)-methanone (synthesis described in EP 707006A). After 18 h the reaction mixture was diluted with 500 ml THF and filtered through a fritted glass funnel with suction. The filtrate was further diluted with ethyl acetate and washed three times with brine. The organic phase was dried with Na2SO4 and concentrated in vacuo. The product was purified by chromatography on silica gel using successively EtOAc/CH2Cl2 (2:1), EtOAc and EtOAc/THF (3:1) as eluents. The product was suspended in hexane and stirred at 60° C. overnight. The mixture was filtered and dried. Yield: 6.2 g of white crystals. M.p.: 222-224° C. [M+1]+=636 and [M+23]+=658

후처리

  1. filtrationfiltered through a fritted glass funnel with suction
  2. additionThe filtrate was further diluted with ethyl acetate
  3. washwashed three times with brine
  4. dry with materialThe organic phase was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by chromatography on silica gel using successively EtOAc/CH2Cl2 (2:1), EtOAc and EtOAc/THF (3:1) as eluents
  7. filtrationThe mixture was filtered
  8. customdried

출처 및 근거

ORD 기록
ord-063ec15f7ef34cbfa82b722640fabf45
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193218B2

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